How many users do you have?

Invariably, when I tell someone about the project I'm working on, they'll ask: â€œhow many users do you have?â€ Sometimes, it'll come up as the first point in a conversation â€” bold, directed, inquisitive. Other times, it'll catch me off guard right in the middle of an otherwise meaningful conversation. This sinful question is the greatest of all conversational sins â€” I myself have been so impertinent as to ask this question of others in the past. But I know now how unmindful it can be.

The question you're really trying to get at is, â€œhow's it going?â€ You want to get a pulse for the progress being made and perhaps how seriously you should take this person's project. But during many phases of a startup's life, user count can be the least significant metric. A better question would be, â€œhow are you currently measuring success?â€ To which the respondent might clearly lay out what is important for them at the stage they're at. They might say: â€œThe most important thing for us right now is making sure we're properly engaging our early adopter base.â€ You might of course be tempted to follow up with, â€œhow large is your early adopter base?â€ but that would again be missing the point. Instead ask â€œOh yeah? And how's that going?â€

The questions you ask largely depend on who you're conversing with. If you meet Mark Zuckerberg and ask him how many users do you have, he'll have no pause telling you â€œthree trillion users and counting.â€ For the rest of us, including founders of early stage products and startups, this number is not always what is most indicative of success. Unless you're hanging out in some hot startup circle where everyone is raising hundreds of millions of dollars and growing by a hundredfold each year, odds are the founders and entrepreneurs you meet will be knee deep in â€œthe struggleâ€. They're experimenting with different strategies and tactics to see what works. They may have a hundred thousand users but only one hundred of them loyal. Or they may have a thousand users with half of them loyal. Your job as a curious interlocutor is not to dig deep into their hard-won business, but to find out what is important to them, and allow them to share that story.

In the circle I hang out with (which is for the most part my wife's friends and their spouses), no one is a millionaire. No one is a wild success story worthy of writing a Wikipedia article about. Everyone does well for themselves, but the majority of us are undergoing â€œthe struggleâ€. At a wedding last night, I was speaking to one such friend who was passionate about the financial markets and teaching strategies to other people. He went on about the methodologies he uses to read charts in a semi-predictable manner, and how the strategy is really clever and intuitive. The easy question for me would have been, â€œWhat ROI are you seeing on your trades?â€ or even more blithely, â€œHow much have you been so far off this strategy?â€ These seem like reasonable questions â€” a man is telling me about a sound financial strategy, and if I am to take it seriously, I should know how well it has faired for him.

But to do so would be to undermine and disregard his lifelong passion for trading and teaching others, and instead reduce him and his life story to a number. It would be to mistake the messenger for the message. Because not everyone you meet â€” perhaps not even most people you meet â€” will be rolling with overwhelming and unstoppable success. Instead of skipping years and years of struggle and asking straight up about the end result, ask about the journey. Ask about the story, the passion, the trials, the challenges, the inspirations, the hard work. Ask about ambitions and goals. Do not feed into the temptation to reduce everyone into a numerical figure. Because that is to entirely miss the point.

Given that, in my experience, the norm is for people to ask immediately about my user count when I tell them about Standard Notes, I notice and admire it when someone is able to have prolonged conversation with me without asking the question. And those conversations tend to be more deep and meaningful.

In recent months, by some irreproducible luck, some of the articles I published on this blog have a received a relatively wide viewership. In some cases it was through an influential person tweeting about it, and in other cases it might have had its fifteen minutes on Hacker News or Reddit. During these episodes, I am ecstatic, and upon sharing the news with my wife, she too is overcome with joy. Wanting to share in my happiness, she checks in often and asks, â€œhow many views??â€ But I don't want to wean her on this question, because truthfully, while this one article may have had a â€œrespectableâ€ view count, I know the next five will probably disappear into nothingness. I understand this concept well, and have come to terms with it. So this number is, for me, an unreliable metric. But, out of all people, I know she truly cares for my happiness, and is inquiring about my view counts not because she wants to reduce my efforts to a figure, but because she wants to understand how I feel about it.

Sensing this, I proposed a better system for communicating emotions about the success or failure of an article: instead of asking me how many views or how many likes, ask me, how do you feel about it? Then I'll take thousands of unseen and ineffable factors and emotions and tell you either, â€œI feel really happy and good about where it's at,â€ or, â€œIt could be better.â€